High polarization ferroelectric liquid crystal compositions
AssigneeDisplaytech, Inc.
InventorsMichael Wand, Xin Hua Chen, William N. Thurmes
Life of this patent
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Abstract
The invention relates to chiral nonracemic liquid crystal compounds having achiral tails comprising a perfluoroalkyl terminal portion which are useful as components in liquid crystal to impart high polarization to the mixture. The materials of this invention can be combined with known liquid crystal host materials to impart improved properties. Chiral nonracemic compounds of this invention can function as additives or dopants in host materials to impart chirality into an LC material.
Claims22
A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:
- CnF2n+1CmH2m—Y—RT-[A]a-[RA]p-[B]b—[RB]q—XCR
- wherein
- n is an integer from 1 to 20;
- m is an integer from 2 to 20;
- a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;
- Y is a single bond or oxygen;
- X is selected from the group consisting of a single bond, oxygen, —CO—, —O—CO—, —CO—O— and a lower alkylene group where one or more carbon atoms is optionally substituted with one or more of oxygen or —CO—;
- CR is selected from the group consisting of:
- wherein
- each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
- R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl,
- provided at least one carbon center indicated by * is an asymmetric carbon center;
- A and B, independently, are linker groups selected from the group consisting of —CO—, —O—CO—, —CO—O—, —CH2—CH2—, —CH2—CH2—O—, —O—CH2—CH2—, —C≡C—, —CH═CH—, and —CH═CH—CH═CH—, and
- RT, RA, and RB together represent a mesogenic core, wherein each of the RT, RA, and RB is independently selected from the group consisting of cycloalkylene, and heterocycloalkylene, cycloalkylene, heterocycloalkenylene, arylene, and heteroarylene each of which is independently optionally substituted with one or more substituents selected from the group consisting of halide, alkyl, haloalkyl, alkenyl, haloalkenyl, nitro, and nitrile.
A compound having the formula:
- wherein
- n and m are integers ranging from 1 to about 20;
- X is selected from the group consisting of a single bond, oxygen, —CO—, —OCO—, —CO—O—2 and a lower alkyl group, wherein one or more carbon atoms of said lower alkyl group is optionally replaced with oxygen or —CO—;
- and
- CR is selected from the group consisting of:
- wherein
- R1 and R3, independently of each other, are hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
- and
- R2 is hydrogen, alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2—, wherein R′ is a lower alkyl optionally substituted with one or more halogens;
- provided at least one carbon center indicated by * is an asymmetric carbon center.
A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:
- CnF2n+1CmH2m—Y—RT—[A]a—[RA]p—[B]b—[RB]q—XCR
- wherein
- n is an integer from 1 to 20;
- m is an integer from 2 to 20;
- a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;
- Y is a singe bond or an oxygen;
- X is selected from the group consisting of a single bond, oxygen, —CO—, —O—CO—, —CO—O— and a lower alkyl group where one or more carbon atoms is optionally substituted with one or more of oxygen or —CO—;
- CR is selected from the group consisting of:
- wherein
- each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
- R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl lower haloalkyl,
- provided at least one carbon center indicated by * is an asymmetric carbon center;
- A and B, independently, are linker groups selected from the group consisting of —CO—, —O—CO—, —CO—O—, —CH2—CH2—, —CH2—CH2—O—, —O—CH2—CH2—, —C≡C—, —CH═CH—, and —CH═CH—CH═CH—;
- and
- RT, RA, and RB together represent a mesogenic core, wherein each of RT, RA, and RB is independently selected from the group consisting of:
- (a) cyclohexylene,
- (b) 6-membered heterocycloalkylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
- (c) cycloalkenylene,
- (d) 6-membered heterocycloalkenylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
- (e) phenylene,
- (f) naphthylene, and
- (g) heteroarylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
- wherein each of RT, RA, and RB is independently optionally substituted with one or more substituents selected from the group consisting of halide, alkyl, haloalkyl, alkenyl, haloalkenyl, nitro, and nitrile.
A compound of the formula:
A non-racemic liquid crystal composition comprising a rod-like chiral liquid crystal compound and optionally an achiral liquid crystal host, wherein said rod-like chiral liquid crystal compound comprises a mesogenic core moiety having an achiral fluorinated alkyl tail on one end of the long axis of said mesogenic core moiety and a chiral tail on the other end of the long axis of said mesogenic core moiety, wherein:
- said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof;
- and
- said chiral tail comprises a chiral moiety selected from the group consisting of:
- wherein
- each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
- and
- R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl;
- provided at least one carbon center indicated by * is an asymmetric carbon center.
A rod-like liquid crystal compound comprising mesogenic core moiety, wherein said mesogenic core moiety is substituted with an achiral fluorinated alkyl substituent on one end of the long axis of said mesogenic core moiety and a chiral substituent on the other end of the long axis of said mesogenic core moiety, wherein:
- said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof, and
- said chiral substituent comprises a chiral moiety selected from the group consisting of:
- wherein
- each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
- and
- R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl;
- provided at least one carbon center indicated by * is an asymmetric carbon center.
Dependencies are inferred from the claim text.